US8309284B2 - Highly conductive organic charge carrier transport material - Google Patents

Highly conductive organic charge carrier transport material Download PDF

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Publication number
US8309284B2
US8309284B2 US12/514,986 US51498607A US8309284B2 US 8309284 B2 US8309284 B2 US 8309284B2 US 51498607 A US51498607 A US 51498607A US 8309284 B2 US8309284 B2 US 8309284B2
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Prior art keywords
transport material
organic
charge transport
charge carrier
highly conductive
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US20100112471A1 (en
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Andreas Kanitz
Jürgen Adler
Ralf Krause
Günter Schmid
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Dolya Holdco 5 Ltd
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Osram Opto Semiconductors GmbH
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1441—Heterocyclic
    • C09K2211/1466—Heterocyclic containing nitrogen as the only heteroatom

Definitions

  • the invention concerns an organic material, in particular, a material which can be used as a semiconductor material or conductive material in organic electronics.
  • Organic semiconductor materials are subdivided into hole and electron transport materials. They are needed for the manufacturing of organic electronic components, such as organic light-emitting diodes (OLEDs), organic field effect transistors (OFETs), and/or organic solar cells.
  • OLEDs organic light-emitting diodes
  • OFETs organic field effect transistors
  • organic solar cells organic solar cells
  • the known materials exhibit deficits both in the bandwidth of the electron injection and also in their stability in the electron-transporting, reduced state, so that, in particular, the radical anions cannot be formed reversibly over a longer time period.
  • the semiconducting characteristics of the materials are attained by doping, because the base materials alone are never conductive enough.
  • One object of the invention is to create an organic electron transport material, in which the bandwidth of the electron injection and also the stability in the electron-transporting, reduced state is improved, in comparison to known materials.
  • Another aspect of the invention is to create a material which can form radical anions reversibly over a longer time period.
  • an efficient electron conductor which is characterized by a larger injection bandwidth and above all, by the capability of forming reversible radical anions of a high stability.
  • One aspect of the invention is directed to an organic charge transport material, with which electrons and holes can be transported equally well, wherein in a layer of the undoped material, with a thickness of 150 nm, a measurable current density of greater than/equal to 0.5 A/cm 2 is already obtained at 0.25 V.
  • the invention can be applied to an organic semiconducting material, which comprises oligophenylenes from heterocyclic parent compounds of the following structure:
  • the layer is thereby transparent, with particular preference transparent in the entire visible spectral range.
  • the current density attained here in the undoped material corresponds to a current density which has been attained up to now only by so-called doped systems.
  • this BPyPyP material can be used directly, instead of an n-doped electron transport matrix, to improve the injection of electrons from the cathode in an organic electronic component.
  • the BPyPyP material is deposited by co-evaporation with n-doping materials or N-doping agents as an even more highly conductive layer.
  • the BPyPyP material is an excellent electron transporter, it is possible to use it in this function in all organic electronic components and arrangements.
  • the material can be used both in OLED arrangements and an ambipolar matrix alone and in any mixtures (blends) for any emitter materials.
  • transparent electrodes can also be produced on any substrates which have the anodic and/or cathodic function, from the material and from mixtures with this material.
  • the excellent current transport appears to come about by a self-organizing, orderly deposition of the molecules by the evaporation process.
  • FIG. 1 shows the current-voltage characteristic curve, from which one can see how the conductivity of the material is manifested in the positive and negative voltage field.
  • FIG. 2 shows the transparency of the material in the UV/VIS spectrum
  • FIG. 3 shows a photoluminescence spectrum of the compound.
  • a typical structure of an organic electronic component comprises a substrate, a lower electrode, the semiconducting organic layer, and an upper anode.
  • the measurement data contained in the figures were obtained.
  • the substrate was made of glass;
  • the lower electrode of indium-tin oxide (ITO);
  • the semiconducting organic layer was a layer of BPyPyP, with a thickness of 150 nm, with a second electrode, above, consisting of an aluminum layer, with a thickness of 100 nm.
  • DMF (200 mL, 2.5 mol, 30 equivalents) is present in a 1000-mL three-neck flask, with a thermometer, dropping funnel, and reflux condenser with a mounted drying tube, and is cooled to ca. 0° C. by means of an ice/salt cooling mixture. While stirring, phosphoroxychloride (46 mL, 0.5 mol, 6 equivalents) is slowly dripped in, wherein the temperature may not rise above 0° C. Stirring is subsequently carried out for 10 min and 1,4-phenylenediacetic acid (16.3 g, 0.08 mol, 1 equivalent) are added to the reactive mixture. Then, the solution is heated to 90° C.
  • the invention concerns an organic, semiconducting material, in particular, a material which can be used as a semiconductor material or a conducting material in organic electronics.
  • a component of the material thereby comprises the oligophenylene from heterocyclic parent compounds with the following structure:

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Photovoltaic Devices (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Light Receiving Elements (AREA)
  • Liquid Deposition Of Substances Of Which Semiconductor Devices Are Composed (AREA)
  • Led Devices (AREA)
US12/514,986 2006-11-14 2007-11-12 Highly conductive organic charge carrier transport material Active 2029-08-03 US8309284B2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE102006053644.4 2006-11-14
DE102006053644 2006-11-14
DE102006053644A DE102006053644A1 (de) 2006-11-14 2006-11-14 Neuartiges hochleitfähiges organisches Ladungsträgertransportmaterial
PCT/EP2007/062210 WO2008058929A1 (fr) 2006-11-14 2007-11-12 Nouveau matériau de transport porteur de charge organique et hautement conducteur

Publications (2)

Publication Number Publication Date
US20100112471A1 US20100112471A1 (en) 2010-05-06
US8309284B2 true US8309284B2 (en) 2012-11-13

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US12/514,986 Active 2029-08-03 US8309284B2 (en) 2006-11-14 2007-11-12 Highly conductive organic charge carrier transport material

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Country Link
US (1) US8309284B2 (fr)
EP (1) EP2092041B9 (fr)
JP (1) JP5193218B2 (fr)
KR (1) KR101482512B1 (fr)
CN (1) CN101679850B (fr)
AT (1) ATE481463T1 (fr)
DE (2) DE102006053644A1 (fr)
WO (1) WO2008058929A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9040175B2 (en) 2010-06-10 2015-05-26 Novaled Ag Electronic device comprising an organic semiconducting material

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102009047880A1 (de) 2009-09-30 2011-03-31 Osram Opto Semiconductors Gmbh Organische elektronische Vorrichtung und Verfahren zu dessen Herstellung
DE102012205945A1 (de) 2012-04-12 2013-10-17 Siemens Aktiengesellschaft Organische Superdonoren mit mindestens zwei gekoppelten Carben-Gruppen und deren Verwendung als n-Dotierstoffe
DE102012217574A1 (de) 2012-09-27 2014-03-27 Siemens Aktiengesellschaft Phosphoroxo-Salze als n-Dotierstoffe für die organische Elektronik
DE102012217587A1 (de) 2012-09-27 2014-03-27 Siemens Aktiengesellschaft Salze des Cyclopentadiens als n-Dotierstoffe für die organische Elektronik
DE102015210388A1 (de) 2015-06-05 2016-12-08 Siemens Aktiengesellschaft Organische Heterozyklische Alkalimetallsalze als n-Dotierstoffe in der Organischen Elektronik
DE102016208298A1 (de) 2016-05-13 2017-11-16 Siemens Aktiengesellschaft Organische elektronenleitende Schicht mit n-Dotierstoff

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0690052A2 (fr) 1994-07-01 1996-01-03 Hoechst Aktiengesellschaft Application de composés conjugués contenant des groupements pyrimidines comme matériaux d'électroluminescence

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Publication number Priority date Publication date Assignee Title
JPS6025973A (ja) * 1983-07-20 1985-02-08 Chisso Corp ピリミジン類
US6147802A (en) 1994-12-28 2000-11-14 Seiko Epson Corporation Polarization luminaire and projection display
CN1064046C (zh) * 1997-11-12 2001-04-04 南开大学戈德防伪技术公司 螺环类光致变色化合物及其制备方法
GB0225244D0 (en) * 2002-10-30 2002-12-11 Ciba Sc Holding Ag Electroluminescent device
KR100573137B1 (ko) * 2004-04-02 2006-04-24 삼성에스디아이 주식회사 플루오렌계 화합물 및 이를 이용한 유기 전계 발광 소자

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0690052A2 (fr) 1994-07-01 1996-01-03 Hoechst Aktiengesellschaft Application de composés conjugués contenant des groupements pyrimidines comme matériaux d'électroluminescence
US5948551A (en) * 1994-07-01 1999-09-07 Hoechst Aktiengesellschaft Use of conjugated compounds containing pyrimidine groups as electroluminescence materials

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
R. Gompper et al., "Synthesis of Oligo (diazaphenyls), Tailor-Made Fluorescent Heteroaromatics and Pathways to Nanostructures", Synthesis, vol. 6, pp. 696-708, 1997.

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9040175B2 (en) 2010-06-10 2015-05-26 Novaled Ag Electronic device comprising an organic semiconducting material
USRE48156E1 (en) 2010-06-10 2020-08-11 Novaled Gmbh Electronic device comprising an organic semiconducting material

Also Published As

Publication number Publication date
DE502007005097D1 (de) 2010-10-28
CN101679850A (zh) 2010-03-24
WO2008058929A1 (fr) 2008-05-22
JP2010509781A (ja) 2010-03-25
CN101679850B (zh) 2013-05-29
KR20090106472A (ko) 2009-10-09
KR101482512B1 (ko) 2015-01-13
DE102006053644A1 (de) 2008-06-12
EP2092041B1 (fr) 2010-09-15
JP5193218B2 (ja) 2013-05-08
EP2092041A1 (fr) 2009-08-26
ATE481463T1 (de) 2010-10-15
EP2092041B9 (fr) 2011-11-09
US20100112471A1 (en) 2010-05-06

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